Sodium Carbonate → HCID 22461192, compound

HRID 1937444Notes

Reaction equation

HRID 1937444 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]([O:13][C:14]([N:16]1[CH:20]=[CH:19][CH:18]=[C:17]1B(O)O)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:5][C:4]1[CH:3]=[C:2]([C:17]2[N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH:20]=[CH:19][CH:18]=2)[CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 115623-BromoanilineHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid

Product 1

HCID 22461192HCID 22461192, compoundYield 41.6%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-bromoaniline (0.48 g), N-tert-butyloxycarbonyl-2-pyrrole-boronic acid (0.6 g), sodium carbonate (0.91 g), tetrakis-(triphenylphosphine) palladium (1.3 g) in DME (30 mL) and water (5 mL) was heated under reflux under argon for 16 h. The reaction mixture was allowed to cool to room temperature and poured into water. It was then extracted with ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate) and evaporated in vacuo. Repeated suction silica gel chromatography eluting with ethyl acetate in hexane (from 10% to 50%, 10% increments) gave desired product as an amber solid (0.3 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under argon for 16 h
  3. extractionIt was then extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated in vacuo
  7. washeluting with ethyl acetate in hexane (from 10% to 50%, 10% increments)

Sources & evidence

ORD record
ord-ca50cb3b00404e87aef6c76ab9c406b7
Source dataset
uspto-grants-2002_05
Patent number
US06395759B1

Reaction notes

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